CH211422A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211422A
CH211422A CH211422DA CH211422A CH 211422 A CH211422 A CH 211422A CH 211422D A CH211422D A CH 211422DA CH 211422 A CH211422 A CH 211422A
Authority
CH
Switzerland
Prior art keywords
production
chrysene derivative
acid
amino
reaction
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH211422A publication Critical patent/CH211422A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/76—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/12—Anthraquinone-azo dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/48—Chrysenes; Hydrogenated chrysenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden, dass ein     Chrysen-          derivat    hergestellt werden kann, wenn. man  1     Mol        2,8-Dihalogenchrysen    mit 2     Mol        1-          Amino    - 5 -     benzoylamino    - 8 -     methoxyanthra-          chinon    umsetzt.  



  Das so in sehr guter Ausbeute erhält  liche Umsetzungsprodukt bildet braunviolette,  kleine Prismen, die sich in konzentrierter  Schwefelsäure mit brauner Farbe lösen und  einen Schmelzpunkt über 4601 besitzen. Auf  Grund der Analyse liegt     Di-(5'-benzoylannino-          8'-        methogy    -1'-     anthrachinonyl)    - 2,8 -     di        arnino-          chrysen    vor. Es stellt ein wertvolles Zwi  schenprodukt dar, das insbesondere zur Her  stellung von Farbstoffen verwendet werden  kann.  



  Die Umsetzung der     2,8-Dibalogenohrysene     mit     1-Amino-5-benzoyl-amino-8-metboxy-          anthracbinon    wird vorteilhaft durch Erhitzen  ihrer Komponenten in     Lösungs-    oder Ver  dünnungsmitteln, wie z. B. Nitrobenzol, Chlor  naphthalin oder     Amylalkohol    und zweck  mässig in Gegenwart von Verbindungen, die  die Abspaltung von Halogenwasserstoff er-    leichtern, wie Kupfer oder Kupferverbindun  gen, sowie von säurebindenden Mitteln, wie       Alkalikarbonaten    und/oder entwässertem Na  triumacetat durchgeführt.  



  <I>Beispiel:</I>  3,8 Teile     2,8-Dibromchrysen,    erhalten  durch     Dibromieren    von     Ohrysen    in     Nitro-          benzol,    7,5 Teile     1-Amino-5-benzoylamino-8-          methoxyanthrachinon,    3 Teile     kalz.    Soda,  3 Teile entwässertes     Natriumacetat    und  0,3 Teile     Kupferchlorür    werden in 72 Teilen  Nitrobenzol verteilt und während 16 Stunden  bei einer Temperatur von 190 bis 2001 ge  halten. Das Reaktionsgemisch wird heiss  filtriert, der Rückstand mit Nitrobenzol, Ben  zol und Alkohol gewaschen und zur Reini  gung mit verdünnter Salzsäure ausgekocht.

    Hierauf wird filtriert, mit Wasser säurefrei  gewaschen und getrocknet.



  Process for the production of a chrysene derivative. It has been found that a chrysene derivative can be produced if. 1 mole of 2,8-dihalochrysenic is reacted with 2 moles of 1-amino-5-benzoylamino-8-methoxyanthraquinone.



  The reaction product obtained in this way in very good yield forms brown-violet, small prisms that dissolve in concentrated sulfuric acid with a brown color and have a melting point of over 4601. On the basis of the analysis, di- (5'-benzoylannino-8'-methogy -1'-anthraquinonyl) - 2,8 - di arnino-chrysenic is present. It is a valuable intermediate product that can be used in particular for the manufacture of dyes.



  The implementation of the 2,8-dibalogenohrysene with 1-amino-5-benzoyl-amino-8-metboxy-anthracbinon is advantageous by heating their components in solvents or diluents Ver such. B. nitrobenzene, chlorine naphthalene or amyl alcohol and conveniently carried out in the presence of compounds that facilitate the elimination of hydrogen halide, such as copper or copper compounds, and acid-binding agents such as alkali carbonates and / or dehydrated sodium acetate.



  <I> Example: </I> 3.8 parts of 2,8-dibromochrysen, obtained by dibrominating Ohrysen in nitrobenzene, 7.5 parts of 1-amino-5-benzoylamino-8-methoxyanthraquinone, 3 parts of calcium. Soda, 3 parts of dehydrated sodium acetate and 0.3 part of copper chloride are distributed in 72 parts of nitrobenzene and kept at a temperature of 190 to 2001 for 16 hours. The reaction mixture is filtered while hot, the residue is washed with nitrobenzene, benzene and alcohol and boiled with dilute hydrochloric acid for cleaning.

    It is then filtered, washed free of acid with water and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Dol 2,8-Dihalogenchrysen mit 2 Mol 1- Amino - 5 - benboylamino - 8 - methoxyantlira- chinon umsetzt. Das so erhaltene Umsetzungsprodukt bil det braunviolette, kleine Prismen, die sich in konzentrierter Schwefelsäure mit brauner Farbe lösen und einen Schmelzpunkt über 460 besitzen. PATENT CLAIM: Process for the production of a chrysene derivative, characterized in that 1 dol of 2,8-dihalochrysene is reacted with 2 moles of 1-amino-5-benboylamino-8-methoxyantliraquinone. The reaction product obtained in this way forms brown-violet, small prisms that dissolve in concentrated sulfuric acid with a brown color and have a melting point above 460. Auf Grund der Analyse liegt Di - (5'- benzoylamino - 8'- methoxy-1' - antbra- chinonyl)-2,8-diaminochrysen vor. Es stellt ein wertvolles Zwischenprodukt dar, das ins- besondere zur Herstellung von Farbstoffen verwendet werden kann. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Umsetzung in Ge genwart von Verbindungen, die die Abspal tung von Halogenwasserstoff erleichtern, so wie von säurebindenden Mitteln durchgeführt wird. On the basis of the analysis there is di- (5'-benzoylamino-8'-methoxy-1 '-antbraquinonyl) -2,8-diaminochrysen. It is a valuable intermediate product that can be used in particular in the manufacture of dyes. SUBCLAIM: Process according to claim, characterized in that the reaction is carried out in the presence of compounds which facilitate the elimination of hydrogen halide, as well as acid-binding agents.
CH211422D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211422A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204241T 1937-06-21
CH211422T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211422A true CH211422A (en) 1940-09-15

Family

ID=25724021

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211422D CH211422A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211422A (en)

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